Interrupted Baeyer–Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate

Article abstract of DOI:10.1002/anie.201712651

The instability of hydroxy peroxyesters, the elusive Criegee intermediates of the Baeyer–Villiger rearrangement, can be alleviated by selective deactivation of the stereoelectronic effects that promote the 1,2-alkyl shift. Stable cyclic Criegee intermediates constrained within a five-membered ring can be prepared by mild reduction of the respective hydroperoxy peroxyesters (β-hydroperoxy-β-peroxylactones) which were formed in high yields in reaction of β-ketoesters with BF₃?Et₂O/H₂O₂.

Full text of DOI:10.1002/anie.201712651

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Accepted Article
Title: Interrupted Bayer-Villiger Rearrangement: Building A
Stereoelectronic Trap for the Criegee Intermediate
Authors: Vera Vil’, Gabriel dos Passos Gomes, Oleg Bityukov,
Konstantin Lyssenko, Gennady Nikishin, Igor Alabugin, and
Alexander Terent’ev
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Interrupted Bayer-Villiger Rearrangement: Building A
Stereoelectronic Trap for the Criegee Intermediate
Vera A. Vil’,[b],[c],[d] Gabriel dos Passos Gomes, Oleg V. Bityukov,
[a]
[b],[d]
Konstantin A. Lyssenko,[e]
[
b]
[a]
[b],[c],[d]
Gennady I. Nikishin, Igor V. Alabugin,* and Alexander O. Terent’ev*
Abstract: The instability of hydroxyl peroxyesters, the elusive Criegee
intermediates of the Bayer-Villiger rearrangement, can be alleviated
by selective deactivation of stereoelectronic effects that promote the
more stable C-O bond.
(CH C(O)OOC(CH OCH ) was characterized by Griesbaum via
NMR and mass-spec data. Anderson reported F NMR and
A
protected derivative of CI
3
3
)
2
3
[
6]
19
1,2-alkyl shift. Stable cyclic Criegee intermediates constrained within
elemental analysis of CF
3
C(O)OOC(CF
3
)
2
ONa [7] whereas Saito
and IR of
a five-membered ring can be prepared by mild reduction of respective
hydroperoxyl peroxyesters (β-hydroperoxy-β-peroxylactones) which
were formed in high yields in reaction of β-ketoesters with
described
1H
NMR
8]
PhC(O)OOC(CH
3
)(CH
2
Bn)OTBDS.[ In addition, a few examples
disclose diverted reactivity where derivatives of the CI were
trapped before rearranging.[9] However, the parent hydroxyl
version of the CI was never isolated and structurally characterized
because of its fleeting stability and high reactivity. In this work, we
will show that stereoelectronic restrictions can be used to block
the 1,2-migration and allow preparation of stable versions of the
Criegee intermediate for structural and mechanistic studies.
3 2 2 2
BF ·Et O/H O .
In 1899, Baeyer and Villiger reported a new reaction that
could convert ketones into esters.[1] More than a century later, this
transformation still continues to provide a valuable connection
between these key organic functional groups (Scheme 1).[2]
This oxygen-rich CI’s structure presents several
stereoelectronic effects.[10] Previously, two such effects were
Furthermore, it displays
a
combination of stereoelectronic
features that can be used to design stereo- and regioselective
processes.[
suggested for the
transformation of the CI into the final product.
moieties include the p-type lone pair of O , the breaking C
bond and the -O acceptor (Scheme 2). The “primary
stereoelectronic effect” requires that the breaking O-O bond and
the migrating C-R bond are antiperiplanar. The “secondary effect”
1 2 3 4
O C O O unit directly involved in the
3]
[
10]-[11]
The key
-R
1
2
m
O
3
4
m
1
is operative when the lone pair of the O H group aligns with the
bond.[
12]
When both effects are in play, an
) to the acceptor is
lone pair assists in breaking the C-
breaking C-R
m
uninterrupted electron flow from the donor (O
ensured: donation from the O
bond by stabilizing the incipient cationic center as the R
1
Scheme 1. General scheme of Baeyer-Villiger reaction.
1
R
m
m
group moves to O
3
and the O
3
O
4
bond breaks. As the result, the
It is generally accepted that the mechanism of Bayer-Villiger
BV) rearrangement involves a tetrahedral intermediate formed by
O
1
=C and R -O bonds are formed.
2
m
3
(
the addition of a peroxyacid to the carbonyl group of an ester (i.e.,
the Criegee Intermediate, or the CI).[4] This high-energy oxygen-
rich intermediate rearranges via an 1,2-alkyl shift that is assisted,
among several factors, by exchange of a weak O-O bond[5] into a
[
[
a]
b]
Gabriel dos Passos Gomes, Prof. Igor V. Alabugin
Department of Chemistry and Biochemistry, Florida State University,
Tallahassee, Florida USA
e-mail: alabugin@chem.fsu.edu
Dr. Vera A. Vil’, Oleg V. Bityukov, Prof. Gennady I. Nikishin, Prof.
Alexander O. Terent’ev
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of
Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
[
phone +7 (499) 1356428; fax, +7 (499) 1355328, e-mail:
terentev@ioc.ac.ru
[c]
[d]
[e]
Dr. Vera A. Vil’, Prof. Alexander O. Terent’ev
D. I. Mendeleev University of Chemical Technology of Russia, 9
Miusskaya Square, Moscow 125047, Russian Federation
Dr. Vera A. Vil’, Oleg V. Bityukov, Prof. Alexander O. Terent’ev
All-Russian Research Institute for Phytopathology, 143050 B.
Vyazyomy, Moscow Region, Russian Federation
Prof. Konstantin A. Lyssenko
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian
Academy of Sciences, 28 Vavilova st, Moscow 119991, Russian
Federation
Scheme 2. Left: Alternative representations of the two stereoelectronic effects
for the 1,2-shift in CI. Right: strategies for weakening the primary and secondary
stereoelectronic effects in the 1,2-alkyl shift
Based on these considerations, we decided to perturb this
system of interconnected stereoelectronic interactions by creating
a constrained cyclic version of the Criegee intermediate where
the “primary” effect is reduced (Scheme 2). Because containment
within a six-membered ring does not stop the rearrangement,[
Supporting information for this article is given via a link at the end of
the document.
13]
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we turned our attention to substrates with a rigid five-membered
cycle. Additionally, we aimed to apply the recently discovered
“
negative” 훼-effect[14] for weakening the “secondary” effect (vide
infra).
Indeed, our computational analysis revealed that the RCOO
dihedral is distorted from antiperiplanarity in the five-membered
peroxylactone (161 degrees, Scheme 2) more than in the six-
membered peroxylactone. This difference suggests that the five-
membered ring may help in diverting the “migrating” bond from
the stereoelectronically favorable alignment with the O-O moiety.
In order to study such systems experimentally, a synthetic
approach to cyclic peroxylactones was needed. Although the
cyclization of ketoesters in the presence of hydrogen peroxide
appears straightforward, the earlier examples were limited in
Scheme 4. Control experiments show stability of endocyclic peroxylactones.
[
15]
2 2 2 4
scope and required harsh conditions (87-98% H O in H SO ).
To overcome these limitations, we developed a milder, more
robust approach towards peroxylactonization by using Lewis acid
The suggested mechanism for the peroxylactonization is
catalysis in the presence of 5% H
2
O
2
(Scheme 3). BF
3
·Et
2
O is
depicted in Scheme 5. The ketoester 1 is initially transformed into
particularly effective in assisting the transformation of β-
ketoesters into the desired rigid five-membered peroxylactones.
Furthermore, the two potential alternative directions for this
process converge on the same product (Scheme 3).
a mixed ketal 5 which further reacts with second H
to form a bis-hydroperoxide 4. The observation that β-hydroxy-β-
peroxylactone doesn’t transform in β-hydroperoxy-β-
peroxylactone 2 clearly shows that cyclization proceeds with bis-
hydroperoxide 4 and not with hydroxy/hydroperoxy compound 5.
Apparently, the cyclic peroxycarbenium ion CPO+ is additionally
destabilized by the carbonyl group. These results are fully
consistent with the computed free energies of the intermediates.
2 2
O molecule
3
2 2
The addition of the first H O molecule to the ketone is endergonic
and the resulting unstable mixed mono-peroxide is only a
transient species. Apparently, formation of the bis-peroxide 4 is
2 2
fast in the presence of the excess of H O . Subsequent cyclization
provides the cyclic bis-peroxide 2, the most stable species at this
reaction hypersurface.
Scheme 3. The peroxidative cyclization of β-ketoesters.
The bis-peroxides
2 (i.e., hydroperoxy peroxylactones)
formed under these conditions represent a peroxy form of CI, with
an exocyclic OOH group instead of the OH moiety. We performed
several control experiments for understanding the product 2
formation (Scheme 4). β-Hydroperoxy-β-peroxylactone 2h does
not equilibrate with β-hydroxy-β-peroxylactone 3h (vide infra)
under these conditions. On the other hand, the β-hydroperoxy-β-
peroxylactone 2h can be prepared in an almost quantitative yield
from an acyclic bis-hydroperoxide 4h (isolated as a minor product
via peroxidation of ketoester 1 at a lower concentration of
Scheme 5. Possible mechanism of Criegee intermediate synthesis and
calculated free energies for the formation of the intermediate structures.
The remarkable stability of the bis-peroxides 2 allowed their
isolation and full characterization. Furthermore, we found that the
exocyclic hydroperoxide moiety in 2 undergoes clean mono
deoxygenation in reaction with triphenyl phosphine. This
breakthrough allowed us to prepare the classic form of the
Criegee intermediates 3 under neutral conditions with a variety of
substituents (Table 1). This finding opens the door for the future
mechanistic studies that can bypass the acid-catalyzed first step
of the BV cascade. This is an exciting opportunity because the
3 2
BF ·Et O). We suggest that low reactivity of these mono- and bis-
peroxides under the acidic conditions stems from the inefficient
stabilization of cationic center by an adjacent peroxide (i.e., the
recently identified “negative intramolecular 훼-effect”).[14] Because
peroxides are less capable of stabilizing cationic centers in
comparison to ethers, peroxide chemistry allows synthetic access
to functional groups that are unstable in their monooxygen
incarnations due to transformations into oxacarbenium ions.
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two steps can have similar activation barriers[16] and the
rearrangement step is not always rate-limiting.[17]
known that α-alkoxy-peroxyesters undergo rearrangement in situ
under acetylation reaction.[20] The peroxy derivative of the Criegee
intermediate is sufficiently stable to be isolated.[ However, once
it is converted into the “normal” OH derivative by an in situ
21]
Table 1. Synthesis of Criegee intermediates 3.[a]
3
reaction with PPh , a fast BV rearrangement occurs (Scheme 6).
3
Scheme 6. Rearrangement of non-cyclic CI can be triggered by PPh .
The computed activation barriers[22] suggest that the non-
catalyzed BV migration of a methyl group is slowed ~700
thousand times (8.3 kcal/mol barrier increase) by inclusion of
peroxide moiety in a five-membered cycle (Scheme 7)! For the t-
Bu and Ph groups that are known to be more prone to migration,
the difference in the barrier height is also significant (~6 kcal/mol,
respectively).
[
a] Combined yields for the two steps.
Nature of the migrating substituent has a dramatic influence
on the stability of Criegee intermediates 3a-j. Whereas the methyl
derivatives 3f,g,h,i are stable, the propyl-substituted compound
3
a was prepared in low yield and only with 90% purity according
to 1H-NMR. Our attempts to isolate the iso-propyl-peroxide 3b
formed by reduction 2b by flash chromatography on silica gel led
to its partial decomposition. Nevertheless, the characteristic
13
Scheme 7. Computational analysis of the 1,2-shfit in acyclic and cyclic CIs.
2
signals of the C(O)OOC(R) OH group in C NMR and HRMS
spectra confirm the formation of peroxide 3b (see SI). On the
other hand, compound 3c with a tertiary (adamantyl) substituent
was unavailable, because even the peroxide 2с could not be
isolated after peroxidation of 1c. The strained peroxide 3d was
also not observed in reaction mixture after reduction of 2d (see
SI). Presence of an acceptor ester group in 3e increases stability
of the β-hydroxy-β-peroxylactone and allows its isolation, albeit in
a moderate yield. Substitution at the α-position does not
compromise stability and the -R-peroxylactones 3f-j were
obtained in 41-58% yields in two steps. These trends in reactivity
It is important to note that, unlike the acyclic CI, the cyclic
peroxyester 3 cannot undergo the 1,2-alkyl shift with the
simultaneous proton transfer that would avoid the formation of a
zwitter-ionic intermediate.[23] The charge separation penalty is
reflected in the ~30 kcal/mol lower exergonicity of the process.
However, this penalty has little effect on the transition state
energy as illustrated by the 1,2-shifts in the analogous six-
membered peroxylactones. The latter systems have activation
barriers that are similar to the acyclic cases, despite having
exergonicity similar to that for the 5-membered cases. The rather
high barriers (~30 kcal/mol for the Me migration) suggest the
importance of acid catalysis for these reactions.
are consistent with the migratory aptitudes of substituents in the
BV rearrangement under acidic[2] and mildly basic conditions[18]
but different from the trends under strongly basic conditions.[19]
To test for the broad utility of the “negative” α-effect[14] as a
Furthermore, the change from the OH to OOH group imposes
an additional protecting effect on the CI by adding an extra 4.4
new stereoelectronic strategy for the control of organic reactivity,
we have also prepared an acyclic model compound 6. It was
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kcal/mol penalty to the 1,2-shift free energy barrier (Scheme 7,
bottom).
Additional insights in the structure and reactivity of 5-
membered CIs were obtained from the combination of
experimental X-ray data and computational analysis (Scheme 8).
Interruption and restarting of the Bayer-Villiger cascade at an
intermediate step opens the doors for future detailed analysis of
the effects of solvents, catalysts, and other additives on the key
migration step that determines the regio- and stereoselectivity of
the overall process. The paradoxical situation where a peroxide is
more stable than its mono-oxygen counterpart illustrates the
power of stereoelectronic thinking in chemistry.
Acknowledgements
Synthesis and experimental studies were supported by the
Russian Science Foundation (Grant № 17-73-10364). Stereoele-
ctronic analysis and computational studies were supported by the
National
Science
Foundation
(Grant
CHE-1465142).
Computational resources were provided by NSF XSEDE (TG-
CHE160006) and RCC FSU. V.A.V. is grateful to Dr. I. A.
Yaremenko for helpful discussions and Department of Structural
Studies, Zelinsky Institute of Organic Chemistry RAS for HRMS
analysis.
Keywords: stereoelectronic control • Bayer-Villiger reaction •
Criegee intermediate • anomeric effect • peroxides
[
[
1]
2]
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correspondent transition states. B: Three (of the four) orbitals involved in the
1
,2-shift for the “level 1” scenario. The C-Rm orbital is not shown. C: Key
nd
geometric parameters from the CI X-ray structures. D: Weakening of the 2
stereoelectronic effect of 1,2-Me shift of OOH versions of the trapped CIs.
Energies in kcal/mol.
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The X-ray geometries reveal an interplay of endo-and exo-
anomeric effects that defines preferred conformations at the
reaction center (Scheme 8 and SI). The endo-anomeric effect
puts the OH pseudoaxial and helps the 1,2-shift by orienting the
migrating group equatorial, so the latter aligns well with the
breaking O-O bond. The exo-anomeric effect[24] aligns the p-type
lone pair of the exocyclic oxygen with the endocyclic C-O bond in
the reactant. This interaction is lost in the TS where the lone pair
reorients to align with the breaking C-C bond to the migrating
group. As the exocyclic OH rotates, the exo-anomeric effect in
reactant is turned off in favor of cationic center stabilization in the
TS. The TS for the 1,2-shift in the five-membered peroxylactones
show noticeably longer Rm-O and O-O distances than the
analogous TS for the less constrained analogues. The structural
differences indicate the loss of C-O and O-O bonding interactions
associated with the weakening of the accelerating
stereoelectronic effects. The NBO analysis confirms that the
donor ability of the OOH lone pairs is significantly lower than it is
for the OH (the 3 and 5 kcal/mol differences in the reactant and
TS, respectively).
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3
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In summary, we disclosed two new strategies for
stereoelectronic trapping of the elusive Criegee intermediate.
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Text for Table of Contents
Vera A. Vil’, Gabriel dos Passos Gomes,
Oleg V. Bityukov, Konstantin A.
Lyssenko, Gennady I. Nikishin, Igor V.
Alabugin,* Alexander O. Terent’ev*
Page No. – Page No.
Interrupted Bayer-Villiger
Rearrangement: Building a
Stereoelectronic Trap for the Criegee
Intermediate
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